Patent GB-418667-A (GB)
Title: Improvements in colouring organic masses capable of being moulded
IPC: C09B33/12
Filed: 1933-03-20
Abstract: Organic masses capable of being moulded such as celluloid, phenol formaldehyde resin and particularly rubber masses are coloured by water insoluble azo dyestuffs free from sulphonic and carboxylic groups which contain the characteristic group R1--X--R2 in which R1 and R2 are identical or different cyclic organic radicles capable of being coupled of which at least one is coupled with an aromatic diazo compound, and in which X is a divalent atom, an atomic group or a diaminoaryl residue.  R1 and R2 may be of aromatic or heterocyclic structure such as from beta-hydroxynaphthoic acid, pyrazolones, and dihydroxyquinoline.  Suitable atomic bridges are --S--, --CO--, --CXX--, (where X is hydrogen or methyl), --NH--, --SO2--, --SO2NH--, --NH--CO--NH--, --NH--CS--NH--, --NH--C6H4--NH--, --HN--C6H4--C6H4--NH--, and --HN--C10H6--NH--.  Dyestuffs mentioned are, o-anisidine, aniline or o-chloraniline (2 mols.) \sQ phenylmethylpyrazolonylurea (1 mol.); o-anisdine (2 mols.) \sQ amino-1-phenyl-3-methyl-5-pyrazolone (1 mol.) and the product treated with phosgene; o-dianisidine (1 mol.) \sQ 1 - phenyl - 3 - methyl - 5 - pyrazolonylurea (1 mol.); o-anisidine (2 mols) or 3-3<1>-dichlorbenzidine (1 mol.) \sQ di-hydroxynaphthoyl-1-5-naphthylenediamide, o-dianisidine \sQ the urea obtained by the action of phosgene on 2-3-hydroxynaphthoic acid -meta- or paraphenylene diamine. Diaminodiphenylcyclohexane (1 mol.) \sQ 1 mol. of the condensation product of beta-hydroxynaphthoic acid (2 mols.) and paraphenylene diamine (1 mol.); diaminodimethoxydiphenyl - cyclohexane (1 mol.) \sQ (1 mol. of) the condensation product from benzidine (1 mol.) and beta-hydroxynaphthoic acid (2 mols.); o-dianisidine or diaminodiphenylcyclohexone \sQ 1 mol. of the condensation product from 2 mols. of beta-hydroxynaphthoic acid and 1 mol. of 4-4<1>-diaminodiphenylmethone; o-dianisidine or diaminodiphenylcyclohexane (1 mol.) \sQ 1 mol. of a condensation product from diaminodiphenylsulphide and 2-3-hydroxynaphthoic acid; diaminodiphenylcyclohexane (1 mol.) \sQ 1 mol. of the condensation product from 2-3-hydroxynaphthoic acid and either diaminodiphenyldimethylmethane or 4 - 4<1> - diaminodiphenylsulphone or diaminodiphenylthiourea; diaminodiphenylcyclohexane (1 mol.) \sQ 1 mol. of the condensation product from 6-amino-2-4-dihydroxy - 1 - N - methylquinoline and 2 - 3 - hydroxynaphthoic acid; o-dianisidine (1 mol.) \sQ 1 mol. of the condensation product from diaminodiphenylamine and 2-3-hydroxynaphthoic acid; diamino-diphenylcyclohexane (1 mol.) \sQ 1 mol. of the condensation product from o-dianisidine and 2-3-hydroxynaphthoic acid; diaminodiphenylcyclohexane (1 mol.) \sQ 1 mol. of the condensation product from 4 - 4<1> - diaminodiphenylsulphonamide and 2 - 3 - hydroxynaphthoic acid. The phenylmethypyrazolonylurea used in the first example is obtained by the action of phosgene on 3<1>-amino-1-phenyl-3-methyl-3-pyrazolone.  The Provisional Specification describes also the use as bridges of --O--, --CO--CO--, <FORM:0418667/IV/1> and <FORM:0418667/IV/2> and includes under R2 malonyl urea, and alpha-methylindol.ALSO:Organic masses capable of being moulded, such as celluloid, phenol formaldehyde resin, and particularly rubber masses are coloured by water insoluble azo dyestuffs free from sulphonic and carboxylic groups which contain the characteristic group R1-X-R2 in which R1 and R2 are identical or different cyclic organic radicles capable of being coupled of which at least one is coupled with an aromatic diazo compound and in which X is a divalent atom, or atomic group or a diaminoaryl residue, R1 and R2 may be of aromatic or heterocyclic structure such as from beta-hydroxynaphthoic acid, pyrazolones, and dihydroxyquinoline. Suitable atomic bridges are -S-, -CO-, -CXX- (where X is hydrogen or methyl), -NH-, -SO2-, -SO2NH-, -NH-CO-NH-, -HN-CS-NH-, -HN-C6H4-NH-, -HN-C6H4-C6H4-NH-, and HN-C10H6-NH-.  A large number of examples are given.